The present invention relates to novel dibenzoyl-tert-butylcarbazonitrile compounds which are highly effective for controlling insect pests and protecting growing plants, trees, shrubs and the like, from attack by such pests. The compounds of the present invention are hitherto unknown substituted and unsubstituted diacylhydrazines useful as insecticidal agents.
A variety of acylhydrazines are known. For instance, 1,2-dibenzoyl-1-alkylhydrazines are disclosed in a paper by Q. N. Porter and A. E. Seif entitled Mass Spectrometric Studies XI Skeletal Rearrangements in Acylhydrazines; published in Aust. J. Chem., 1972, 25, 523-9. Similarly, 4-nitrobenzoic acid 2-benzoyl-1-(1,1-dimethylethyl)hydrazine is described by Maerky, Michael, Meir et al., in a paper entitled The Photochemistry of Sydnones and 1,3,4-oxadiazolin-2-one, Helv. Chem Acta, 1978, 61(4), 1477-510. Again, no utility is reported for this compound.
Although Japanese patent application JP-050819, filed 17-4-80, publication No. J5 6,147,066 describes N,N'-dibenzoyl-N,N'-dialkyl-alkylenediamines for detecting blood in body fluids, insecticidal use of the disclosed compounds is neither described nor suggested.
In a Nissan Chemicals Industry Ltd. Japanese patent application JA-091048, filed 11-9-72 publication No. J4 9,047,528, benzoylhydrazine derivatives as acaricidal agents are disclosed. This publication does not suggest or disclose benzoyl-tert-butylcarbazonitriles for control of insects. The Nippon Soda Co. Ltd Japanese patent application JA-020216, filed 18-3-69, publication No. JA 7,302,770-R, describes a number of N-substituted-N-phenylhydrazines and indicates that these compounds exhibit insecticidal and miticidal activity. The publication does not, however, describe or suggest that dibenzoyl-tert-butylcarbazonitriles are effective as insecticidal agents.
Offenlegungsschrift DE No. 3228631 describes 1-phosphorylthioacetyl-2-acyl-hydrazines as insecticidal, acaricidal, fungicidal and nematocidal agents. These compounds are only remotely related to the compounds of the present invention since they are acylhydrazines but contain a phosphate or thiophosphate function.
Although intermediates useful in the preparation of the dibenzoyl-tert-butylcarbazonitriles of the present invention are described in U.S. patent application Ser. No. 926,779 filed Nov. 12, 1986, the compounds disclosed do not, however, contain a cyano function, nor is the introduction of a cyano function obvious from, or suggested by, the above-said application. Moreover, the substituted and unsubstituted dibenzoyl-tert-butylcarbazonitriles of the present invention are unexpectedly effective as a systemic insecticidal agents against larvae and crop protection agents.
It is an object of the present invention to provide novel substituted and unsubstituted dibenzoyl-tert-butylcarbazonitrile compounds useful in controlling a wide variety of insect pests and protect growing plants, trees, shrubs and the like from attack by said pests.
It is a further object of the present invention to provide methods of preparing the compounds of the invention and methods of using said compounds as insecticidal agents. These and other objects of the present invention will become evident by the detailed description of the invention hereinbelow.